3,4,5-Trihydroxy-benzoic acid (2R,6R)-4-carboxy-2,4,6-trihydroxy-cyclohexyl ester

ID: ALA39744

Chembl Id: CHEMBL39744

Cas Number: 110170-37-1

PubChem CID: 475263

Max Phase: Preclinical

Molecular Formula: C14H16O10

Molecular Weight: 344.27

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 4-O-Galloylquinic Acid | 4-O-Galloylquinic acid|4-Galloylquinic acid|110170-37-1|CHEMBL39744|(3R,5R)-1,3,5-trihydroxy-4-(3,4,5-trihydroxybenzoyl)oxycyclohexane-1-carboxylic acid|HY-N8592|BDBM50469566|AKOS040761136|FS-8014|CS-0148677|F86500|(3R,5R)-1,3,5-trihydroxy-4-(3,4,5-trihydroxybenzoyl)oxy-cyclohexanecarboxylic acid|(1S,3R,4S,5R)-1,3,5-Trihydroxy-4-((3,4,5-trihydroxybenzoyl)oxy)cyclohexane-1-carboxylic acid|(1S,3R,4S,5R)-1,3,5-Trihydroxy-4-[(3,4,5-trihydroxybenzoyl)oxy]cyclohexanecarboxylicShow More⌵

Canonical SMILES:  O=C(O[C@H]1[C@H](O)C[C@](O)(C(=O)O)C[C@H]1O)c1cc(O)c(O)c(O)c1

Standard InChI:  InChI=1S/C14H16O10/c15-6-1-5(2-7(16)10(6)19)12(20)24-11-8(17)3-14(23,13(21)22)4-9(11)18/h1-2,8-9,11,15-19,23H,3-4H2,(H,21,22)/t8-,9-,11-,14+/m1/s1

Standard InChI Key:  OGYBSNRRBNHPNK-FTBFGRRBSA-N

Alternative Forms

1. Parent:

   

   ALA39744

   4-O-Galloylquinic acid

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 344.27

Molecular Weight (Monoisotopic): 344.0743

AlogP: -1.34

#Rotatable Bonds: 3

Polar Surface Area: 184.98

Molecular Species: ACID

HBA: 9

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.92

CX Basic pKa: ┄

CX LogP: -1.11

CX LogD: -4.67

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.26

Np Likeness Score: 1.88

References

1. Kilkuskie RE, Kashiwada Y, Nonaka G, Nishioka I, Bodner AJ, Cheng Y, Lee K.  (1992)  HIV and reverse transcriptase inhibition by tannins,  2  (12): [10.1016/S0960-894X(00)80422-9]

2. Kashiwada Y, Nonaka G, Nishioka I, Ballas LM, Jiang JB, Janzen WP, Lee K.  (1992)  Tannins as selective inhibitors of protein kinase C,  2  (3): [10.1016/S0960-894X(01)81072-6]

3. Kashiwada Y, Nonaka G, Nishioka I, Chang JJ, Lee KH..  (1992)  Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.,  55  (8): [PMID:1431932] [10.1021/np50086a002]

Source

Source(1):

• Scientific Literature